Sodium Acetate → HCID 20294038, compound

HRID 1413208Notes

Reaction equation

HRID 1413208 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7](Br)[S:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[H][H]>CO.[Pd]>[C:1]([NH:4][C:5]1[N:6]=[CH:7][S:8][C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 20294040HCID 20294040, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20294038HCID 20294038, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-acetamido-2-bromo-5-methylthiazole (2.3 g) and sodium acetate (0.8 g) in methanol (60 ml) was hydrogenated at atmospheric pressure over 10% Pd/C catalyst until the theoretical uptake of hydrogen had occurred. The catalyst was removed by filtration and washed with methanol and the filtrate was evaporated to dryness. The residue was extracted with hot CCl4 and the extracts were evaporated. The residue was recrystallised once from petroleum ether (b.p. 60°-80° C.) and once from hexane to give 4-acetamido-5-methylthiazole (0.2 g) m.p. 62°-4° C. (Found: C, 46.6; H, 5.3; N, 18.1. C6H8N2OS requires C, 46.1; H, 5.2; N, 17.9%).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. customthe filtrate was evaporated to dryness
  4. extractionThe residue was extracted with hot CCl4
  5. customthe extracts were evaporated
  6. customThe residue was recrystallised once from petroleum ether (b.p. 60°-80° C.) and once from hexane

Sources & evidence

ORD record
ord-22d19c4025634d7f981e69f51c507b4e
Source dataset
uspto-grants-1981_02
Patent number
US04249012

Reaction notes

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